Trigalloylglucose

Details

• Internal ID: c4d3fadf-41a4-431a-beca-8fbea6b8459a
• Taxonomy: Lignans, neolignans and related compounds > Dibenzylbutane lignans
• IUPAC Name: (3S,4S)-3,4-dihydroxy-3-(3,4,5-trihydroxybenzoyl)-1,5-bis(3,4,5-trihydroxyphenyl)-4-[(1R,2R)-1,2,3-trihydroxypropyl]pentane-1,2,5-trione
• SMILES (Canonical): C1=C(C=C(C(=C1O)O)O)C(=O)C(=O)C(C(=O)C2=CC(=C(C(=C2)O)O)O)(C(C(C(CO)O)O)(C(=O)C3=CC(=C(C(=C3)O)O)O)O)O
• SMILES (Isomeric): C1=C(C=C(C(=C1O)O)O)C(=O)C(=O)[C@@](C(=O)C2=CC(=C(C(=C2)O)O)O)([C@@]([C@@H]([C@@H](CO)O)O)(C(=O)C3=CC(=C(C(=C3)O)O)O)O)O
• InChI: InChI=1S/C27H24O18/c28-7-17(35)24(42)26(44,22(40)9-3-13(31)20(38)14(32)4-9)27(45,23(41)10-5-15(33)21(39)16(34)6-10)25(43)18(36)8-1-11(29)19(37)12(30)2-8/h1-6,17,24,28-35,37-39,42,44-45H,7H2/t17-,24-,26+,27+/m1/s1
• InChI Key: UHDJFCOJSFPKML-UOAHBSSISA-N
• Popularity: 63 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₄O₁₈
• Molecular Weight: 636.50 g/mol
• Exact Mass: 636.09626391 g/mol
• Topological Polar Surface Area (TPSA): 352.00 Ų
• XlogP: -2.50
• Atomic LogP (AlogP): -2.27
• H-Bond Acceptor: 18
• H-Bond Donor: 14
• Rotatable Bonds: 11

Synonyms

• SCHEMBL15667245

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8016	80.16%
Caco-2	-	0.8937	89.37%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6518	65.18%
OATP2B1 inhibitior	+	0.5839	58.39%
OATP1B1 inhibitior	+	0.8400	84.00%
OATP1B3 inhibitior	+	0.9504	95.04%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.4566	45.66%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.8045	80.45%
CYP3A4 substrate	-	0.5427	54.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7925	79.25%
CYP3A4 inhibition	-	0.7601	76.01%
CYP2C9 inhibition	-	0.8728	87.28%
CYP2C19 inhibition	-	0.9215	92.15%
CYP2D6 inhibition	-	0.9156	91.56%
CYP1A2 inhibition	-	0.6684	66.84%
CYP2C8 inhibition	-	0.8070	80.70%
CYP inhibitory promiscuity	-	0.9355	93.55%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8432	84.32%
Carcinogenicity (trinary)	Non-required	0.6806	68.06%
Eye corrosion	-	0.9954	99.54%
Eye irritation	-	0.8185	81.85%
Skin irritation	-	0.7660	76.60%
Skin corrosion	-	0.9332	93.32%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6787	67.87%
Micronuclear	-	0.5008	50.08%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.6218	62.18%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.9139	91.39%
Acute Oral Toxicity (c)	III	0.7360	73.60%
Estrogen receptor binding	+	0.7156	71.56%
Androgen receptor binding	+	0.7428	74.28%
Thyroid receptor binding	-	0.5886	58.86%
Glucocorticoid receptor binding	-	0.4875	48.75%
Aromatase binding	-	0.5154	51.54%
PPAR gamma	+	0.6931	69.31%
Honey bee toxicity	-	0.9373	93.73%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.8814	88.14%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.35%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.89%	99.17%
CHEMBL2581	P07339	Cathepsin D	89.73%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.06%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	87.06%	94.73%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	84.59%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.35%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.51%	89.00%

Plants that contains it

• Arctostaphylos uva-ursi
• Fragaria × ananassa
• Punica granatum

Cross-Links

• PubChem: 90116889
• LOTUS: LTS0254126
• wikiData: Q104397747